


Get down boy, go head get down

by SageMasterofSass



Series: Requests [5]
Category: Black Sails
Genre: Aftercare, Anal Sex, Barebacking, Bottom!Flint, D/s undertones, Domesticity, Flint is his customer, Light Bondage, Light Spanking, M/M, Mafia!Flint, Non-Negotiated Kink, Oral Sex, Orgasm Delay/Denial, PWP, Rough Sex, Silver being gagged, Smut, Vane and Eleanor are Silver's pimps, Weapons Kink, both the tense and POV change, minor blood play, not really tho, prostitute!Silver, request, some fluffy emotions crept in there too sorry about that, the second chapter includes all of the above as well as
Language: English
Status: Completed
Published: 2015-07-23
Updated: 2016-02-27
Packaged: 2018-04-10 18:47:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 10,040
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4403129
Author URL: https://archiveofourown.org/users/SageMasterofSass/pseuds/SageMasterofSass
Summary: <blockquote class="userstuff">
              <p>To fill the following prompt;</p><p>prostitute client au flint/silver</p>
            </blockquote>





	1. Captain/Prostitute AU

**Author's Note:**

> Yes, the title is totally reference to Kanye's Gold Digger. For obvious reasons. 
> 
> So I realized like 2000 words into this that I could have modernized it? I'm regretting not doing that. I'm also seriously considering just writing a modernized version anyways and slapping a second chapter onto this for the fun of it. We'll see; I already have like fifty projects open and unfinished right now.

Flint had never been a fan of whore houses. It had nothing to do with the principal of it and more to do with the actual whores within, whose low cut bodices and short skirts had never seemed appealing to him.

On the odd occasion he had run across rent boys, they were just that, _boys._

He was not a man who enjoyed fucking children, thank you very much.

So when Max herself, mistress of the Nassau whorehouse, came to fetch him mere minutes after his boots had hit sand, he wasn’t terribly enthusiastic about listening to her offer.

“Trust me,” she said, accent thick and cloying as she threaded one of her arms through his. “I thought of you the moment I purchased this whore. You won’t be disappointed. I’ve even considered selling you the contract. For an inflated price, of course, I have to make a profit after all.”

On Flint’s other side, Billy glanced at the woman, then his Captain and shrugged his broad shoulders. “I can see to the men,” he offered.

Flint sighed, eyes rolling heavenward. If he didn’t give in, Max would simply keep at him until she got what she wanted. Better to get it out of the way quickly, see this whore she had bought and dismiss her so that he could get on with the business he needed to see to in town.

“Lead on,” he relented, allowing Max to tow him in her wake.

Other captains and various men of import enjoyed doing business in Max’s brothel, so Flint was familiar with both the building and most of its inhabitants. He’d met the girls at least once each, and subsequently pushed them off his lap, out of his way, or brushed aside wandering hands. They smiled pleasantly as taught when he was near, but no longer bothered trying to approach him.

That is, of course, except for Max herself. She slipped slender fingers into his shirt, emerging with a single gold piece, though she was lucky to keep the hand at all.

“Insurance,” she winked, tucking the coin into her bodice before gesturing him towards the staircase. “Preparations have already been made in the far room on the left.”

Flint eyed her distrustfully but ultimately decided it was not a trap of some sort; his men brought too much business to her doors and with how successfully he ran his ship, they all had plenty of gold to spend when they did. Unless she’d been paid off, she had no reason to try and turn against him.

His boots echoed against the wood of the stairs as Flint climbed them, the din and music of the room below fading slightly as he reached the upper story. The door to the room at the end of the walkway was closed but not locked when he reached it.

The sight he opened it to gave him pause.

He had been expecting something else entirely.

For one, a woman.

The man stretched out on the bed greeted Flint with a small smirk and nothing else. He was naked but for that smirk, propped on his side with his head on his hand. His position was not poised but a natural sprawl, one leg tucked behind the other and his free hand resting open and relaxed against the sheets.

“Well,” he drawled after a moment, “either come in and close the door, or leave.”

Flint came in and closed the door behind him, adding that final barrier so that the noise of the whorehouse finally abated to a soft murmur on the edges of his mind.

The room was close and shadowed, the only furnishing being the bed and thick drapes hung beside the window. Being only a few hours past noon though, the sun was high and the light filtering through the glass was more than enough to see by.

“So you are Captain Flint then,” the whore said, sitting up on the bed and cocking his head to the side. It caused his thick head of dark curls to shift, their ends brushing broad, tanned shoulders.

“I am.” Flint stepped further into the room, letting his gaze skim over the body on offer.

Once past his initial surprise, he could admit a faint gratitude that Max had fetched him immediately. The man was certainly not a rent boy, but there were plenty of customers who would not have cared about the well toned muscle or thick cock, just wishing to indulge in a willing hole.

Flint, though. He could appreciate those things, and more. Like the hint of a beard, the thick, wiry patch of pubic hair, the roughness around the man’s edges that suggested he was once a laborer of some kind, the sharp intelligence of his pale gaze, the twist of his full lips that was both arousing and infuriating.

“My name is John Silver,” the whore replied. “Max says that everything in this room tonight is on the house so please, make yourself at home.”

The words were polite, the tone amused like Silver was in on a joke that Flint had yet to figure out. Those pale eyes tracked the captain as he rounded the bed, fingers tugging buttons loose on his shirt and then unlacing his breeches. He took the time to fold each garment as it came off, placing his boots by the wall with the finished pile of fabric, the air of the room warm against his bared skin.

Silver gave a soft hum, his eyes tracking over Flint’s body much the same way Flint had observed him before.

Flint couldn’t help cocking an eyebrow. “Like what you see?”

“So far?” The whore raised an eyebrow of his own before obviously ogling where Flint was half-hard against his thigh. “Yes, I rather do.”

It had been a long time since Flint had felt this kind of arousal; he was not going to waste it. “Are there things you won’t do?” he asked briskly, business like.

That got him an amused expression and a faint laugh. “Well, I’m not going to let you piss on me if that’s what you mean,” Silver said.

“Not what I meant,” Flint growled, stepping up to the bed for the sole purpose of sliding his fingers to the nape of Silver’s neck and then gripping the hair there, hard. Tugging caused the whore’s head to tilt back, throat arched and lips parted.

“I want to know if I can use you how I please.”

Watching Silver’s pupils visibly dilate, black eating away bright blue, was fascinating. He licked his lips, swallowed hard, said “Yes” on a soft exhale.

It was the most submissive Flint had seen him since walking in the door, and the grin pulling across his lips felt feral. He didn’t kiss Silver, but he did lean down to trail teeth and tongue over that vulnerable neck, pausing wherever he could feel the whore’s pulse under his skin and biting bright red marks there that would purple before Flint ever left tonight.

Silver’s body was taut under him, but pliant, and when Flint released his handful of hair the man slumped, shoulders loose, eyes blown. Pushing him from the mattress down to the floor was a simple task, Silver going to his knees easily. He stared up from under thick lashes, mouth curling up into something dirty and self satisfied even as he leaned into Flint’s space, calloused hands sliding along hairy thighs.

Flint carded one hand back into Silver’s hair, fingers tight in the curls, and the other he slipped under Silver’s jaw, tilting his chin up so that the whore was forced to look him in the eyes. It was an obscene sight, all that tanned, lithe muscle at his feet, waiting for his command but looking like he might not follow it just to see if Flint would punish him.

“Max offered to sell your contract to me,” he said conversationally, tilting Silver’s face this way and that in his grip as if examining an object he wished to purchase.

“Is that so?”

“If you can satisfy me I might even consider it.” A lie, he was already trying to figure out exactly how much Max would want for him.

Silver just smirked. “And what’s in it for me if you buy my contract?”

“Well, you won’t have to be fucked by all those men downstairs for one.”

“Maybe I like being fucked,” Silver countered.

“A born whore then,” Flint returned. “If you’re that greedy for cock, I’ll consider letting my crew have a few rounds with you. The men get testy after too long at sea, after all.”

Still smirking, Silver made a small noncommittal noise, swaying forward so that his chin pressed just below the jut of Flint’s hip. He could faintly feel that hot breath against his skin as the whore spoke, all arrogance just asking to be put under Flint’s thumb. “Is there a reason you’re only talking about other men fucking me instead of doing it yourself?”

“I’m still deciding if you’re worth it,” Flint said without missing a beat. “Suck my cock and then I might fuck you.”

He released Silver’s chin and the first thing the man did was turn and bite at the meat of Flint’s thigh, not enough to hurt or bruise, just a cheeky nip that had Flint’s hand tightening in Silver’s hair. “Yes, captain.”

Throughout their conversation, Flint hadn’t lost his chub, but he hadn’t hardened any further either. Under Silver’s ministrations he was fully hard in a matter of minutes, those plump lips trailing up and down his length, tongue flickering out to taste here and there and pressing into his foreskin.

Flint sighed when that mouth finally closed around him properly, sucking gently at the head before venturing lower. Silver bobbed a few times, curls bouncing around his face and cheeks hollowing out the lower he went before taking the entirely of Flint’s prick down in one go, pausing with his nose buried in coarse, red hair.

Then he started swallowing, throat working smoothly along Flint’s cock and the captain couldn’t help his guttural groan. Silver’s eyes fluttered open from where he’d closed them, bright under his lashes, and Flint brushed the whore’s hair from his face just to take that picture in; pink lips split wide around his dick, tanned skin flushed, blue eyes watering slightly from strain.

“God, look at you,” he murmured, pressing on one cheek to feel himself in that plush mouth. “Fuckin’ made for this, weren’t you?”

Silver swallowed once more before pulling back, saliva dribbling over his lips and down his chin as he gasped for breath. He didn’t look wrecked just quite yet, but it wouldn’t take much effort to get him to that point.

“On the bed,” Flint ordered, voice low and rough, and Silver grinned up at him despite the way his lashes were clumped together with unshed tears.

“Oh, did I pass the test then?”

“You won’t if you don’t get your ass on the bed.”

The whore laughed before getting to his feet and crawling onto the mattress. Silver glanced over his shoulder, knees tucked under himself and his back a long, lean line. “How do you want me?”

Flint considered the question before deciding, “Hands and knees.”

“Original,” Silver teased, but he made himself comfortable in the center of the bed, knees spread and upper body braced on his elbows, so that his ass was in the air. From this point of view, the insides of his thighs were shiny and slick, a wet trail leading up to where he was already stretched and loose.

“Max’s orders?” Flint questioned, kneeling behind the whore and tracing that oiled path.

Shivering under the touch, Silver leaned back into it. “Not really. It’s standard; some men would rather take you dry than wait for you to prepare yourself.” He glanced over his shoulder, only one blue eye visible, framed by those thick, dark curls. “Also, I was getting bored up here all by myself.”

Imaging the act was easy enough; Silver stretched out on his back on the bed, three fingers buried in his ass, hips arched, his other hand wrapped round his dick and pulling urgently. Maybe he even made himself come once or twice before Flint ever arrived.  

“Play with yourself often?”

Silver merely sighed, so Flint laid one hand against the small of the man’s back, and used the other to swat his ass, one side then the other. The skin pinkened under the blows and Silver’s back arched, head coming up with a gasp.

“I asked you a question,” Flint said, smoothing over the marks he’d made with a palm open in obvious threat.

“Yes,” Silver breathed, settling back down onto the bed. “Yes, I do.”

“Tell me what you do,” Flint demanded, trailing his fingers down to that open hole, finding the flesh warm and wet and giving. Fuck but that was nice.

The whore trembled, breath audibly catching in his throat. “I,” he started, sounding breathy and desperate, “I slick up my fingers, work them in one at a time.”

“How many did you get to before I came in?”

Silver groaned softly when Flint teased at his rim, circling it with the tips of two fingers before pressing in just enough to make the muscle give, and then retreating again.

“Four. I got to four.”

Flint sucked in a breath between his teeth. “Fuck. And are they better than a cock, your fingers?”

“ _God_ no.”

Resisting the urge to simply slam into the whore and then proceed to pound him into the mattress was getting difficult, but Flint restrained himself if only for the pleasure of teasing Silver further. He slid two fingers into that unresisting body, watched the way Silver shuddered and sighed, felt how he clamped down on the intrusions as if trying to draw them deeper inside.

“Tell me how much you want it,” Flint ordered. “Tell me how much you want my cock.”

Silver merely groaned, dropping his forehead against his arms, so Flint circled his fingers until he found the tight bundle of nerves that had the whore gasping, body growing tight as a strung bow.

“Tell me,” he repeated, pressing mercilessly on Silver’s prostate until the man was whining and twitching under him.

“Sadistic bastard,” Silver cursed at him, and then, “Goddamnit, just fuck me already! I want your cock in me, you asshole.” The words were coupled with a small rolling of his hips, the whore spreading his knees wider on the bed and pushing his ass out, his own prick heavy and red and weeping where it bobbed between his legs.

“Don’t touch yourself,” Flint told him. He spread the whore’s ass and pressed his cockhead against Silver’s hole, not allowing himself to sink into the tempting heat, just resting there until Silver was whining again, trying to push back against the faint pressure.

Again, Flint slapped his ass, pleased by the man’s surprised yelp and the angry pink of the abused skin. Then, while Silver was recovering from the surprise of the hit, he thrust into him with one harsh roll of his hips, the force of it knocking the bed loudly against the wall.

Silver moaned under him, spine tensing then going liquid as Flint set up a quick, punishing rhythm, not giving either of them time to adjust to the other. The sound of skin striking skin quickly filled the air between them, Flint gritting his teeth as sweat broke out along his inner thighs, the small of his back, the hollow of his throat, under his arms, and Silver arching into the captain’s bruising hold on his hips, moans wanton and urgent.

“Fuck,” the whore cursed when Flint ran a hand up his back and then gripped his hair tight, forcing his head back and his spine to arch. It gave Flint extra leverage to strengthen his thrusts until each one was knocking the breath out of the man beneath him, along with a myriad of soft whimpers.

The power of the position, the control it gave him, was heady. Flint could feel his muscles straining, pleasure sizzling from his core outwards with Silver clamping hot and tight around him. He was velvety soft inside, so that each thrust was more of a glide, and Flint was able to push himself deep into it, balls slapping against Silver’s ass.

Silver started meeting him movement for movement, and Flint slowed his pace to allow it until they were more or less rocking together, tempered and sinuous. 

“God, your _cock,_ ” Silver moaned. “So fucking deep.”

Flint tightened his grip in those curly locks, forcing Silver to bare his throat further. “You like that, little whore?”

He couldn’t see Silver’s eyes dilate, but he could practically hear it in the breathy, “Yeah,” that he murmured.

“Like being split open?” Flint punctuated the question with a particularly hard thrust of his hips, pushing the whore further up the bed and making his “ _Fuck yes,_ ” hissed and tight.

Drapping himself over Silver’s back, Flint released his hair, using that hand to support his weight and the other to reach under the whore and grab his cock. It made Silver shudder and cry out, especially when Flint buried his teeth in the back of Silver’s neck, but he simply squeezed the man’s prick to keep him from coming before Flint was ready for him to.

The new position made his thrusts more shallow and awkward, but they were both close by this point. Flint released the back of Silver’s neck, licking at the dark imprint his teeth had left behind and feeling a surge of heat go through him when he realized he’d actually pierced skin in a few places, small beads of blood welling up under his tongue.

“Let me come,” Silver groaned, clawing at Flint’s wrist to try and get him to loosen his hold.

Flint smirked and only squeezed again, making Silver’s breath whoosh out of his chest, his intake of air noisy when Flint let up on the pressure.

“Not yet,” he admonished. “Not until I’ve come first.”

“Gonna come inside me?”

Another squeeze to Silver’s cock. “Why? Do you want me to?”

The whore groaned long and low, part pleasure, part frustration. “Yes.”

“Then you can come after I’ve filled you up.”

With that, Flint levered himself back up, releasing Silver’s cock to put two hands on the whore’s hips. If he came before Flint did, well, he’d get the chance to punish the man after all.

Guiding Silver’s hips counterpoint to his own movements, Flint fucked into him hard and fast, paying little to no attention to the other man’s pleasure and simply taking his own from Silver’s body. It took only a minute until he groaning, head tipping back as he came, cock buried deep and pulsing into the whore’s ass.

For a long moment he stayed there, allowing himself to catch his breath. When he pulled out, he did it slowly, watching in satisfaction as a combination of oil and cum followed in his wake, leaking down towards Silver’s balls. He realized the man was shaking, probably so close to coming himself that it was practically painful.

“May I?” Silver asked, and Flint was tempted to call him a good boy for his obedience, stroke his hair from his face and soothe that bite mark. Instead, he told him he may, and scooped up the escaped cum on his fingers and pressed it back into that silky heat.

Silver didn’t even have to touch himself, he just came against the sheets, cock jerking and a high, desperate noise escaping his mouth. Then he just laid there, still shaking slightly and looking completely debauched, hair twisted and tousled from Flint’s thick fingers, bite mark stark against the back of his neck, ass red from being spanked, and cum still dripping lazily from his used hole.

Flint sat back and admired his work, wiping his fingers on Silver’s thigh to clean them. The whore didn’t even twitch.

The captain left him like that after dressing, though Silver did eventually curl up onto his side instead of sitting with his ass in the air.

When he came downstairs, Max was waiting for him looking smug and self-satisfied.

“Well?” she asked.

“I want his contract.”

She smiled, dark eyes bright as she held up a familiar looking pouch in her fingers. “You’ve already paid.”

Flint stared at it for a second before patting down his chest and when that revealed nothing, pulling his collar from his skin and peering at the inside of his shirt. Sure enough, the small pouch of gold he carried within it (kept separate from the ship’s as it was personal funds) was missing.

“How-“ he started angrily, but was cut off by tanned arms slipping around his neck and a still naked body pressing against his back.

“Sticky fingers,” Silver breathed into his ear, sounding highly amused. “Never trust a whore, Captain Flint.”

There was not a moment of their encounter where Flint could imagine Silver getting into his belongings. He shook the man off and turned to glare at him, even as Max handed over a thick sheaf of paper.

Silver still looked well fucked and was obviously basking in his afterglow, his grin loose and easy. It was this reason Flint blamed for the way he accepted the papers without complaint, making Silver’s smile widen.

“I’m all yours, captain.”


	2. Mafia/Escort AU

**Notes for the Chapter:**

> And here's the possibly final chapter? I dunno, we'll see, I'm kind of really loving all the different AU possibilities here. At the very least, this is the last chapter for a while because I have a million other things I need to try and finish before I go off to college again. 
> 
> Enjoy the depravity, friends. I think I'm really getting the hang of filthy writing.

One of the best things about expensive hotels is that they keep a widely varied stock of expensive alcohol on hand at all times.

A single call down to the front desk has a bottle of Angel’s Envy bourbon delivered into Silver’s waiting hands not even ten minutes after he puts the phone down. It typically costs over three hundred dollars per bottle, but the hotel has an inflated price that’s closer to five hundred.

Silver hums as he pours himself a glass on the rocks, perfectly content and comfortable in the lavish room with its highline view and ridiculously large bed. Outside large windows, New York city lights shine against a backdrop that suggests darkness along its edges, but is too lit up to actually be black.

The room itself is filled with honey light that compliments the warm brown and red color scheme it sports, and Silver traces over the familiar lines as he downs his first glass. He’s used to a lavish life style, but even so he never gets quite as lush an experience as he does whenever James Flint calls on him. That’s what happens when you get hired by one of the most influential members of the mafia in the entire city, possibly the state.

And since Flint has all that money, and is willing to spend it? Silver takes it upon himself to spend it for him, as much as humanly possible in a single night. He insists on meeting at The Ritz -meaning Flint always has to pull strings to get them a reservation on short notice- staying the night, and ordering one of their more lavish breakfast spreads in the morning. And of course the expensive alcohol, like the Angel’s Envy. Last time they met up, Silver had ordered wine that had been over a thousand dollars. Needless to say, Flint hadn’t been amused by Silver’s little game.

Then again, Flint is rarely amused by Silver’s games. Which doesn’t necessarily mean he doesn’t like them, of course. They give him perfect cause to punish the escort as Flint sees fit.

Silver can unabashedly say he likes a little punishment.

He pours his second glass and drinks this one a little more slowly, savoring the heavy, dark flavor and the burn of the drink crawling down his throat. Honestly he doesn’t look like he belongs here, in this room, with this bourbon in hand. Not in his plain button down and too-tight jeans, his VANS and messy hair and golden complexion.

Flint though. Flint always looks like he belongs. When he strides purposefully through the door as Silver is starting on his third glass of the night, there’s no exception. He’s wearing a charcoal grey three piece suit, his maroon tie an enticing splash of red against the white of his undershirt. As always he is immaculate and powerful looking, hair tied severely back and stubble looking artfully unshaved.

“Took you long enough,” Silver comments, setting his glass down with a small clink on the dark wood bureau.

Flint closes the door behind himself and gives the room a quick visible inspection. (Always the paranoid one, but Silver can’t really fault him for it.) When he’s done he turns those shrewd eyes on the escort, one side of his mouth twitching up into something that’s not quite a smile.

“What did you order this time, John?”

He smirks, lifts his glass and swirls it pointedly in Flint’s direction. “Bourbon. Want some?”

Flint approaches and takes the glass from him, gaze never leaving Silver’s even as he swallows what’s left of the contents, expression fixed in that stone cold scrutiny.

“You’re supposed to let the ice melt a little before pouring,” he admonishes when he’s finished, and Silver just gives an unconcerned shrug.

“Like I would know that. Now, are you going to let me undress you?”

Flint steps away from him, but then makes a lazy ‘go ahead’ gesture that reminds Silver of kings waving despondently at something a peasant has said. It sends shivers down his spine.

Now, Silver loves a lot of things about his rendezvous with Flint, but his absolute favorite thing is getting to undress the man of all his weapons. He likes to try and predict how many Flint will have on him based on what news is being passed around the underground; the more serious shit gets, the more weapons Flint carries, and vice versa.

Also, there’s just something unbearably sexy about pulling each deadly object off a man who could so easily pluck that weapon out of his grip and use it against him. Call him a masochist.

Lately, the underground has been abuzz with talk about a massive drug deal that’s going to be going down, so Silver is hoping Flint is packing.

He goes to his knees, pushing up the loose, pressed fabric of Flint’s dress pants to get at the gun strapped right above his ankle. It’s small, a .22, which is more of a warning than an actual threat. On the other side of that same holster is a thin knife, the edge jagged and the tip sharp enough that Silver watches his fingers carefully as he pulls it out so as not to lose them. This particular blade doesn’t appear unless things are truly going to shit and Silver lays it and the .22 carefully on the bureau before going back to unstrap the holster itself and set it aside as well.

During the whole process, Silver touches a little more than he probably should, sweeping his fingers over exposed skin, and Flint watches him with dark, inscrutable eyes that don’t waver in their intensity for even a second.

Silver finds two more knives strapped to the opposite leg, one down low and one up on the thigh (and god, the thigh holsters are so fucking attractive), another gun pressed securely against his ribs, this one a .45 with intricate tooling all over the handle that Silver can’t help but run the tip of his tongue over, a bowie knife hidden in the lining of his jacket, copious amounts of excess ammo also in his jacket, and a pair of thick, heavy brass knuckles that Silver weighs in the palm of his hand before picking up and studying the rough finish to the metal, the edges that will cut and tear as a fist slides off the point of contact. He licks his lips, tempted to rub those edges, where he thinks he can see faint blood stains, lightly over his skin, watch the sharp peaks catch and tear at the first few layers without injuring him.

But he sets them aside as well and then stands patiently in front of Flint who, despite Silver asking to undress him, is still completely clothed.

Flint observes him for a second, then states, “You missed one.”

Silver flicks his gaze up and down the man’s body, looking for where he could have missed something else being stashed, before Flint calmly reaches under his waistcoat and slips out a long knife, the handle as thin as the blade so that it laid flat against his torso.

Silver bites his lip, watches those competent fingers twirl the knife absent-mindedly before securing it in a loose, easy grip.

He’s expecting the way Flint crowds him back against the bureau and grabs his face in a tight grip, the force of it pushing his jaw open. There will be punishment for missing that last knife, and he’s not disappointed when the cold metal of it meets his bottom lip, the edge digging in just enough to sting.

Silver shivers when he licks at the blade, the taste thick and metallic on his tongue. He knows what Flint wants, what he’s waiting for, so he presses harder with his tongue, slips it between the knife and his lip so that it slices into the delicate skin. Warm copper blooms slowly around the metal, but Flint doesn’t retract the blade until Silver’s mouth is wet with blood, red droplets threatening to slide down his chin.

Flint’s eyes are dark where they’re fixed on the escort’s mouth, their green color all but swallowed by pupil. Silver’s not sure where the knife ends up after it’s pulled away, but he doesn’t particularly care because Flint’s lips come down over his. It’s not exactly a kiss though; it’s more Flint keeping Silver’s jaw open with the strong fingers still gripping his face and then licking into him, lapping up blood and biting at Silver’s lips with harsh teeth.

Staying still under the onslaught, Silver relaxes into it and closes his eyes. The smooth drag of Flint’s tongue sends little spikes of heat intermittently through him and he can’t help scraping his own teeth against it, threatening to bite but not going through with the act for the way it makes Flint press tighter against him, physically pining him to the hard wood at his back. He presses so hard Silver’s back ends up bowed, arched under the larger man’s weight, and he’s sure to have bruises where the edge of the wood is unforgiving against him.

Only when the cut on Silver’s tongue refuses to give up any more blood does Flint finally back off. He considers the escort for a moment before turning his back and beginning to strip his coat off. It’s a silent command for Silver to get undressed as well, and he does so with gusto. His jeans were starting to get tight and uncomfortable where he was growing hard inside them, the denim rough against sensitive skin because he hadn’t bothered with underwear.

Whereas Silver just shucks all his clothing off, leaving it to lie in a discarded pile and then flop happily onto the bed, Flint takes considerably longer.  He hangs his jacket neatly on the back of a chair, lays his vest over it, folds his shirt and slacks and sets them in the seat, socks pressed neatly into shined shoes. The first time Silver had seen this little ritual, he’d teased Flint about it for ages, but he’s grown inured to it by now and only smirks to himself at the man’s obsession with order and control.

What he’s never quite grown used to is Flint’s body. Toned by working within the mafia, his appearance well-maintained, he looks damn near sculpted with thick, ropy muscles and a spattering of red-brown hair across his chest, under his navel, and down his powerful thighs. He looks dangerous and rugged released from the sharp confines of his suit, and Silver kind of really loves it, can’t help but lick his lips when Flint finally approaches the bed with his maroon silk tie in hand.

“On your stomach,” Flint tells him, standing over the mattress and raking his eyes over Silver, as if contemplating exactly where he wants him. “Hands crossed behind your back.”

Silver obeys the command, stretching out in the middle of the bed flat on his stomach with his wrists at the small of his back. He’s rewarded by the feeling of smooth silk drawing tight around his wrists. There’s a cool drag of the tail along his spine, the excess of the tie left to pool and he wonders if it’s maybe long enough to wrap around his throat as well. Probably not, but maybe next time he’ll bring a few supplies of his own and send Flint the bill for them.

Flint doesn’t direct him from there, just comes around the side of the bed to dig lube out of the bedside table (bless expensive hotels). Then there are warm hands mapping down Silver’s back, smoothing along the dip of his spine, the dimples above his ass, the gentle almost non-existent curve of his sides. The bed dips behind him as Flint kneels on it, pushing Silver’s thighs apart so he can situate himself between them.

He hums slightly at the questing fingers, their touches teasing and flighty, surprising him in a new place every time they appear before he finally hears the pop of the lube cap and feels slick liquid being dripped onto his ass. Then the fingers are more sure, rubbing lube into his rim, slipping into his body for a brief second only to retreat again. It continues like this for a while, until Silver is squirming, trying to press back onto them only for Flint to smack his ass every time he tries.

“C’mon,” he whines, twisting his fingers into the silk on the opposite wrist so that he has something to hold onto. “You’re killing me here.”

Another slap, this one with decidedly more sting. “Am I going to have to gag you?”

Silver can admit that the idea does make him salivate more than a little. “That depends,” he says, twisting a little to try and peer over his shoulder and then giving up when he can’t quite manage the position. “How long do you intend on teasing me?”

Of course he doesn’t get an answer to the question, Flint isn’t particularly chatty until they really get into things, and then he gets down right verbose with his dirty talk. Filthy promises and a heavy possessiveness that Silver will never admit gets him off almost more than anything else the man does to him, and all in that heavy, rough voice of his, like water on dark rock.

“Maybe I’ll invest in a ball gag,” Silver goes on when Flint only continues to tease him open. “Or one of those O-ring gags? The kind you can push your dick through. I’ll get a blindfold to match it too, maybe some handcuffs so you don’t keep ruining your ties.”

This time he gets a grunt and the bed shifting under him as Flint leans over his body. “Chin up,” he says, and when Silver complies something cool and soft is forced between his lips. It’s the same red of the tie, Flint’s handkerchief then, he thinks, and it’s not long enough to be tied around the back of the head so it’s simply inserted as a crumpled up ball, keeping his mouth open almost uncomfortably wide.

“That’s better,” Flint breathes before pushing Silver’s face back down to the mattress roughly. It makes breathing a little difficult but the escort wouldn’t complain if there was a knife at his throat (honestly, that’d just make this already fantastic situation even better).

Flint sits back, but rather than return to his teasing, warm hands close around Silver’s hips and flip him effortlessly onto his back. His arms and hands end up trapped underneath his body, forcing his hips up, and it’s already starting to put a strain on his shoulders, but still he doesn’t make a sound.

His cock is achingly hard, arched up towards his chest and flushing an angry red. Even in the few seconds Flint takes to appraise him, pre-cum drools from the tip and collects in the hair beneath Silver’s navel.

He bends his knees and plants his feet on the mattress to relieve some of the weight off his hands, thighs spread wide, and Flint twists one of his nipples in reprimand for moving without being instructed.

Silver would argue the punishment if, A) he didn’t arch and moan unashamedly into it, and B) there wasn’t currently spit-coated silk in his mouth. The pleasure-pain is a good distraction for the discomfort of laying on his arms, so much so that he doesn’t even notice Flint slicking up his own dick with lube because those thick fingers are still twisting and flicking at his nipple, making it red and puffy until it throbs deliciously.

“You like that, boy?” Flint asks when he lets up, only to notch his dick against the escort’s hole and _push,_ knocking Silver’s breath out of his chest before he can think of giving some sort of response. It doesn’t hurt, but Flint hadn’t really put a lot of effort into prepping, so after the first inch or two it does grow uncomfortable.

“Fuck, you’re tight.”

Silver squirms, enjoying the sensation of being too full too soon as Flint threads his arms under the escort’s knees to give himself more leverage. When they’re finally flush, a small sweat has broken out on Flint’s forehead and Silver is breathing heavily through his nose, saliva slipping past the soaked rag in his mouth.

His arms and shoulders ache, his hands are starting to go numb from a combination his own weight and the slightly too tight binding, it’s difficult to breathe with his mouth so full, his chest is still throbbing, and it seems like his ass is not far behind.

Honestly, Silver’s afraid he’s going to come a little too soon at this rate.

Flint pulls all the way out, a thick, slick noise following the slow movement sending heat prickling across Silver’s skin. Then the hands resting behind the escort’s knees tighten and Flint slams home again, rocking them both up the bed and pulling a guttural noise from deep in Silver’s chest. He tosses his head back, eyes closing, only for Flint to twist his already abused nipple again, making him gasp and snap his attention back on the man moving between his legs.

“Pay attention,” Flint says, nearly pants as he sets up a quick tempo of his hips. The sound of squelching lube is filthy loud around them and Silver has to fight the urge to let his eyes roll back in his head in pleasure.

“Are you listening?” Another pinch to his nipple and Silver nods his head empathetically, back arching so he can meet Flint’s thrusts. The man makes a noise of approval then, “You’re not allowed to get off, do you understand me? I’m going to fuck you, and I’m going to come in your ass, and then I’m going to take a break and drink that bourbon you got, but I’m going to leave you tied up and you won’t say a fucking word about it. Then, once I’m good and ready, I’ll fuck you again. Won’t even have to lube up because you’ll still be wet from the first round, my cum dripping out of your used hole.”

Silver can’t help moaning his enthusiastic consent, hooded gaze fixed on Flint’s intense one.

“Use you all night, for as long as I want, won’t I, boy?”

He tries to say yes around the gag, but just makes an embarrassingly high-pitched noise instead. He loves when Flint gets that possessive look, when his fingers grip too tight and his thrusts too hard.

“You got anyone else who fucks you like this?”

 It’s because of that possessiveness and how hot it makes Silver, that he _doesn’t_ have anyone else. He’s an escort, he’s paid to have sex with near strangers, but ever since he met Flint? He’s been dropping his other clients like flies, unwilling to stand the touch of clammy hands and sloppy mouths when he’s had a taste of something so much fucking better.

Of course, his manager Vane hadn’t been terribly happy with the decision. Even less happy with it was the real head of the operation, Eleanor (Vane just being her incredibly hot but equally intimidating and insane figurehead), but Flint pays just enough for Silver’s services to keep the escort on the books without any serious problems. If Silver could, he’d quit altogether but, well, he doesn’t exactly have any other skill sets and he rather likes this lavish lifestyle, thanks.

So, when he shakes his head no in answer to Flint’s question, he’s being completely truthful. Which just makes the flash of dark pleasure across the man’s face that much sweeter.

It only takes a couple more bed-shaking thrusts for Flint to come, his hair knocked free of its careful tie and sticking to his sweaty skin, cock pulsing, and breath shuddering out of his chest in harsh pants. His movements slow gradually, until he’s simply braced over Silver on the bed, their bodies still joined and the escort shivering underneath him.

True to his word, Flint hardly even glances at Silver when he finally levers himself up, only picks himself up off the bed and runs a hand through his hair, loosening the rest of it. He collapses splay-legged into a chair and drags the bourbon and a glass of ice towards himself.

While Flint relaxes and has a drink, Silver can feel cum and lube slipping out of him, can feel the strain in his arms and shoulders and where his hands are starting to go numb. His dick is so hard it hurts, a veritable pool of pre-cum across his taut stomach, his left nipple angry and red. He’s coming down from his endorphins, slowly but surely, and with it comes a heavy sense of discomfort and varying levels of pain. In the position he’s in, he’s sure his muscles will start to lock up sooner rather than later, but he’s positive if he tries to move at all, Flint will simply making him wait around even longer.

So he spends thirty minutes prostrate on the bed as Flint goes through several glasses of bourbon, uses the in-suite restroom, cleans the blade that still has Silver’s blood on it, and then finally, _finally,_ casually wanders over and sits on the edge of the mattress.

“Can I trust you enough to take the gag out?”

At Silver’s nod, Flint carefully pries the ruined handkerchief from his mouth, the fabric sodden and near-dripping when he sets it on the bedside table. Silver swallows the excess saliva in his mouth, licks his lips, and works his jaw a few times to try and soothe the ache.

Flint watches him, and when Silver keeps quiet, he gives a small approving smile.

The escort gets Flint hard again with his mouth, finding the twinge in his jaw at having it forced wide again just this side of pleasurable. Flint pets at his face, not exactly encouraging but certainly not discouraging either, until he pulls out and slides down the bed.

“You look good like this,” Flint comments, pushing Silver’s thighs even further apart and Silver cocks an eyebrow.

“Well-fucked?” he risks asking.

“Completely debauched.” Thankfully Flint doesn’t seem keen on punishing him for speaking out of turn and is more focused on lining his cock up and pressing gingerly into Silver’s body. He’s still wet and lose from earlier, but even so he’s already a little sore and is glad the other man is moving so slowly.

Thirty minutes before had been a quick, dirty fuck, but this is definitely softer, Flint’s gaze fixed on where they’re connected, probably watching how his own cum collects along his dick as he moves.

Silver’s erection had wilted a little while waiting, but it doesn’t take long before his cock is hard and weeping once more.

“Am I allowed to come this time?” he asks, and can’t help how hopeful he sounds.

Flint, the asshole, smirks at him but then assents with a throaty, “Yes.”

It’s a huge relief, and Silver allows himself to melt into the mattress, as much as he can anyways, and simply enjoy the slow, thick drag of Flint inside him. When he closes his eyes and tips his head back, baring his throat, Flint doesn’t reprimand him, but a large hand does close around the escort’s neck. It’s a light pressure, doesn’t impede his breathing so much as suggest that it could, which is exciting in its own way.

There’s no squelching lube or flesh slapping flesh, just their labored breathing and Silver’s soft moans, Flint’s occasional groan and grunt. But it’s just as hot, and Silver finds himself reaching his orgasm long before Flint ever does, spine bowing, lips parted, cock jumping and spurting cum all the way up his chest. He shudders through it, but Flint hardly reacts, doesn’t change his rhythm in the least.

The escort’s afterglow hits him pretty hard, has him nearly liquefying, drifting in the haze of his own mind as Flint continues to use his body. By the time the other man has come for a second time, Silver is still slightly out of it, though not enough to not feel the warmth in his lower body, the cum sliding out of him in Flint’s wake.   

Sex with Flint is fucking fantastic of course, the best Silver has ever had, but it’s not the only reason he’s stopped seeing other clients. Despite his gruff exterior, his controlling nature, he pleasure in causing pain, Flint is actually rather amazing with after care. It’s not something the escort could ever say about…well, pretty much anyone else he’s ever slept with, man or woman. He’s a prostitute after all, he doesn’t need after care, right?

Flint either doesn’t think so, or doesn’t care. He turns Silver over onto his stomach and carefully undoes his bindings, helping him stretch his arms out slowly and bring feeling back to them, then wets a washcloth in the bathroom and wipes them both down.

Silver is just rousing enough to sit up and flex the rest of his body to work the kinks out when Flint pours them glasses of bourbon. They sit and drink together, quiet after the activity and noise, and when only ice meets their lips, Flint licks the lingering taste of the alcohol out of the escort’s mouth, lingering and almost sweet.

They end up curled together on top of the blankets, the only light coming from the city outside, and Silver thinks again of telling Flint about how he’s not seeing anyone else anymore but decides against it. He knows that in the morning, when he wakes, Flint will be gone, but in a few days time, a week at most, Silver will have another voicemail waiting for him on his phone, asking for another meet up.

It’s enough for him.


	3. Businessman/Prostitute AU (bottom!Flint)

**Notes for the Chapter:**

> I got a request for bottom!Flint and since this fic was already under way, I figured I'd tweak it a bit to fill the request! (The only way it was going to be different was Silver bottoming from the top lmao) 
> 
> Anyways, enjoy. It's not as porny as the other two chapters?? It actually feels kinda domestic, oops. It's also shorter, so sorry about that.

James Flint leads a stressful life.

He’s pretty high up in the corporate food chain, but not quite high enough to really keep his ass out of the constant fire that is executive life. It’s all meetings and managing the people beneath him and being managed by the few who actually sit above and sending out emails and checking revenue and listening to pitches and filtering through all the shit the employees give him to find the actual good material. Basically it’s just exhausting, okay? He doesn’t even have a personal life at this point, but you know what? That’s alright.

There’s only one need he has that isn’t filled by a typical day in the office, and that’s his libido. And that? Well, that’s easy enough to fill.

“Going to do what I say, James?” a voice breathes into his ear, and he shivers in response.

There’s a heavy, warm weight against his back, his wrists tied firmly to the headboard above him. But that’s the way he prefers it, trapped on his stomach with Silver pressing in close behind him.

Teeth graze against the shell of his ear, light and teasing, and he shifts his head to the side to give Silver more room to work with. Which is why, of course, the other man backs off immediately, chuckling lowly.

“You’re always so needy,” he says, smirk evident in his voice as he trails cool fingers down Flint’s bare back. “’Course you always are when you call me. Have to be in order to hire a hooker just to fuck you senseless.” Silver pauses and sighs, like he’s thinking before he picks up again. “Who even does that? Typically you hire a hooker because _you_ want to fuck something, but nooo, not James Flint. No, he needs something…different.” The last word is soft and full of promise, and Flint groans lowly.

“Get on with it already!” he snaps, even as he pulls on his bindings just to feel their bite.

Silver laughs again, shifting away so that Flint can no longer feel his heat or weight. “Needy, but impatient,” he remarks with amusement, and suddenly his hands are on Flint’s thighs, slowly working their way up.

Then he feels lips, a single kiss brushing against him before Silver decides to bite instead, working his way up one hair-dusted thigh and then down the other, taking his time like he has nothing better to do with his day than bruise Flint up. His facial hair is rough and makes Flint’s skin prickle with sensitivity everywhere it brushes against him, until he’s twisting in the sheets, thighs spread wide to try and encourage that mouth up where he really wants it.

Again though, Silver pulls back, a single finger tracing over the marks Flint’s sure he’s left behind. “Man, you’re even worse than usual today,” he muses quietly, even as Flint buries his face in the mattress and groans. “You’re already pretty close to begging, aren’t you? Usually it takes a while to get you to that point. Must have had a stressful week, huh?”

Flint’s beyond the casual small talk at this point, but he knows the soft cadence of Silver’s voice is supposed to ground him, calm him down a little. He breaths deep and fights the urge to grind his hips into the mattress where he’s already hard. He won't beg. Not today. 

“I really wanted to play,” Silver continues, sounding almost mournful. “But that’s not really what you need, is it?”

His idea of play is usually to eat Flint out until his whole body is lose and pliant and his ass is red with stubble burn, or to flip him over and ride him painstakingly slow, teasing, edging him on, before fucking him almost brutally. Flint’s a fan of both, but he doesn’t have the patience for either today. Luckily, Silver seems to understand because there’s the sound of a bottle cap opening, and then cool, slick fingers are opening Flint up quickly and with little teasing.

He sighs and relaxes against the intrusions, glancing briefly over his shoulder to see Silver leaning over him, expression concentrated as he watches what he’s doing. His dark hair is falling over his face, and he keeps having to tuck wayward strands behind his ears before they simply fall loose again. Flint’s always found him attractive, with his charming smile and strong build, but he’s at his best when he’s bent over like this, completely focused on tearing Flint apart and building him anew.

Within a few minutes, those glorious fingers pull out and leave Flint feeling almost unbearably empty. He knows that Silver didn’t prep him enough, that the first slide in is going to sting, but Silver knows that too, and he knows just how much Flint loves it, even needs it at times.

Silver rests a hand casually against Flint’s thigh, a touch to keep him grounded while he tears a condom open with his teeth and slides it on. He doesn’t bother asking if Flint is ready or not, if he wasn’t he would have said something already, and just pushes in with a painstaking slowness that makes Flint grit his teeth hard. Instantly there are warm palms sliding up his sides.

Silver leans over him, pelvis snug against Flint’s ass as he slides that last inch inside, and murmurs, “Relax,” right against Flint’s ear.

His muscles loosen almost on instinct upon hearing the command, his body relaxing against the mattress and Silver sighs upon feeling it. “Good,” he says, then pushes himself up on his palms and delivers the first slow, deliberate thrust.

It all goes to hell after that. Flint was right, as soon as Silver starts moving there’s a definite burn radiating through the pleasure, but it’s so _good._ And after that first thrust? Well, it was the last of Silver’s slow movements, that’s for sure. He pounds into Flint hard and fast, skin slapping skin and breath coming heavily, that burn melting into something liquid hot and amazing as Flint gasps beneath him.

Unable to help himself, Flint arches into it, presses his hips back and up so that Silver’s cock slides along his prostate on every other stroke. His fingers are claws in the sheets, eyes flickering between wide open but unseeing, and squeezed tightly shut.

“Fuck,” he hears Silver mutter above him, and the man slows his pace until he’s rolling his hips languidly, a fluid, practiced motion. The heat coming off of him is so much more intense now, and when his chest brushes against Flint its slick with sweat.

“Why’d you stop?” he mumbles, his arms falling lax from where they were gripping the bedding tight.

Silver gives a breathless little laugh, and he thrusts once, harshly, says “I haven’t stopped, in case you haven’t noticed,” before returning to his smoother rhythm.  

Flint groans, rubs his face into the sheets. “Might as well have,” he grumbles and feels the way the other man stiffens slightly behind him.

There’s a harsh release of breath, and then Silver is slamming into him. _Hard_. “So,” he grits, pulls out, slams in again with so much force Flint thinks he might bruise from the impact, “needy!”

Silver’s movements are knocking the air right out of Flint’s lungs, but if they weren’t he’d be moaning loud and long. As it is he can’t do much more than whine high in his throat as Silver keeps hammering into him, mouthing off as he goes about how he never gets a break whenever Flint hires him, about how demanding Flint is, how much Flint must love having all his control stripped from him, methodically and piece by piece.

It’s that final comment, hissed between gritted teeth, that pushes Flint over the edge. He comes hard against the mattress without his dick having received any stimulation aside from being trapped beneath his body weight. His whole body seizes with it, twitching with pleasure as soft sighs tumble from between his lips, eyes fluttering closed.

Behind him, Silver pauses for a moment, his breathing heavy and loud in the space between them. “Did you just come?” he asks incredulously. Flint kind of jerks his head both in acknowledgement and agreement, and Silver huffs a little.

“Well that’s a first.”

True, but Flint can’t even feel his legs or arms yet he’s so blissed out, so he can’t exactly comment on the oddity. Usually though, Silver is the first to come and he either makes Flint get him hard again, or brings out some toys to fuck Flint with instead. For Flint to come first? Well, his week was really _really_ bad, okay?

Silver takes a second to catch his breath before leaning back and pulling out slowly. He’s still hard, Flint can tell that much by the way he hisses slightly as he rolls the condom down and throws it away. But obviously it doesn’t bother him much, because he gets up and walks around to the headboard to untie Flint.

“Stay there,” the other man says, like Flint really has the energy or motivation to do much more than pull his sore arms close to his body. Either way, Silver disappears and returns a minute later with a cool rag that he runs down Flint’s body, wiping away sweat and lube.

By the time he’s done, Flint has rolled over out of his own mess and thrown one arm over his face, breath evening out and lengthening though he’s not in danger of falling asleep. The easy caress of the rag leaves, but its replaced by the bed dipping under Silver’s weight as he crawls up next to him.

After a moment of silence Flint finally admits, “They were threatening to fire me.”

Silver doesn’t respond, but long fingers do start to card through Flint’s hair. He takes a moment to reveal in the feeling before he shakes the touch off and sits up on the bed.

He’d been right before, Silver is still hard where he’s lounging casually beside him, though he doesn’t look like he’s even thinking about it anymore. Instead he’s watching Flint with a mixture of curiosity and compassion that the man isn’t entirely comfortable with.

“Come here,” Flint says, voice coming out gruffer than intended.

The look Silver gives him is confused, but he does shuffle closer, and then raises his eyebrows when Flint makes himself comfortable between his thighs.

“You don’t have to-“ he starts, but Flint cuts him off with a succulent, “Shut the hell up.”

He goes down on Silver with a quiet fervor, licking a wet path up his cock and then taking it down deep and sucking hard. It makes the man’s hips hitch even as he groans loudly, fingers back in Flint’s hair though this time they’re holding him tight and not comforting.

Flint pulls against the hold, enjoying the pressure and faint pain even as Silver’s dick slides repeatedly down his throat, a thick, full glide. (He’s long since trained his gag reflex into obedience.)

It doesn’t take long to get Silver off, not with the way he’d been fucking into Flint earlier. He comes down Flint’s throat with a muffled curse and Flint stays there, swallowing repeatedly to work him through it. Only when Silver starts to get too sensitive does he back off, licking at his lips and taking in the large breaths of air that he’d been denied.

Silver’s fingers slip from his hair as Flints sits up, and the other man spends a moment with his head thrown back, eyes closed as he recovers. When he does lift his head, bright blue eyes find Flint immediately, and Silver just smirks tiredly.

“You’re fucking weird,” he says, and Flint rolls his eyes in response.

They’re both tired but they also know that in an hour or two they’ll be ready for the next round. After that, Silver will fall asleep in Flint’s bed, and even though Flint will kick him out come morning with a handful of cash and not even a shower, tonight they’ll curl up together under the sheets like one of them isn’t a prostitute and the other his customer.

In the meantime, Flint levers himself to his feet and hunts down a pair of clean boxers and some sweatpants. “Take-out okay?”

Silver considers for a second then shrugs his shoulders. “I can cook, if you’ve got anything besides frozen dinners.”

Not likely, but Flint might just have a few things lying around. “I’ll look. Clean up though, I’m not letting you in my kitchen when you look like that.”

The other man snorts and waves him off, and Flint can hear him rummaging through his drawers for something clean to wear as he heads to the kitchen.

**Author's Note:**

> I take requests on my [tumblr](http://scribespirare.tumblr.com/). Not all requests get 3k words though, only the ones I really like.


End file.
